• Canadian rapper had huge bet on boxing legend to win
  • This isn’t the first time Drake has lost big when betting
  • Jake Paul beat Mike Tyson on a unanimous decision
Drake Monica Lewinsky
Drake Credit: Imago

In the aftermath of the hugely hyped Jake Paul – Mike Tyson event last weekend, it has emerged that Canadian rapper Drake has lost a huge sum after betting on the wrong man to win.

Backed wrong man

Drake is reported to have lost $355,000 by betting on Tyson to win the fight, which took place last Saturday at the AT&T Stadium in Arlington, Texas. Had Tyson emerged victorious, Drake could have pocketed more than $1 million.

The Paul–Tyson fight was broadcast live on Netflix – although it was beset by technical problems. In the event, which went the right-round distance, 27-year-old Paul beat 58-year-old Tyson on a unanimous decision.

Drake is known for liking a bet on big sporting events – and fights like Paul v Tyson – but he is also developing a reputation for losing his bets too. In recent times, Drake has lost more than $2 million betting on sports events. In 2022, he lost hundreds of thousands of dollars betting on France to beat Argentina in the FIFA World Cup final. Drake also lost $400,000 in another Paul bout – this time when he lost to Tommy Fury.

Fortunately, Drake’s music career success means that he can afford to lose bets like this. Back in June, the Canadian became the first music artist to reach 100 billion streams on Spotify – including performances as a lead artists and featured artist. 

McGregor called out

But Drake wasn’t the only person to bet on the wrong man last weekend. UFC legend and actor Conor McGregor also backed Tyson only to have to rip his ticket up when the result was announced.

McGregor has been touted as a potential next opponent for Paul who, after beating a near-pensioner, is looking for his next fight. Paul called McGregor out the day after the fight on X (which everyone still calls Twitter) for an MMA bout. Given McGregor is older than Paul and retired, it could happen.

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Dan Parton
Dan Parton is an experienced journalist, having written about pretty much everything and anything during the past 20 years - from movies to trucks to tech. Away from his desk, he is an avid movie and sports watcher and gaming fan.